Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806038645/hk2131sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806038645/hk2131Isup2.hkl |
CCDC reference: 624730
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.061
- wR factor = 0.144
- Data-to-parameter ratio = 17.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: WinGX (Farrugia, 1999).
C24H19NO4 | F(000) = 808 |
Mr = 385.4 | Dx = 1.365 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3059 reflections |
a = 10.0396 (5) Å | θ = 2.3–28.3° |
b = 9.8912 (5) Å | µ = 0.09 mm−1 |
c = 18.9631 (9) Å | T = 100 K |
β = 94.965 (3)° | Block, yellow |
V = 1876.04 (16) Å3 | 0.2 × 0.13 × 0.09 mm |
Z = 4 |
Bruker X8 APEXII 4K diffractometer | 4606 independent reflections |
Graphite monochromator | 3462 reflections with I > 2σ(I) |
Detector resolution: 512 pixels mm-1 | Rint = 0.046 |
φ and ω scans | θmax = 28.4°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −13→13 |
Tmin = 0.982, Tmax = 0.992 | k = −12→13 |
13970 measured reflections | l = −25→25 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.061 | w = 1/[σ2(Fo2) + (0.0588P)2 + 0.8797P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.144 | (Δ/σ)max < 0.001 |
S = 1.08 | Δρmax = 0.34 e Å−3 |
4606 reflections | Δρmin = −0.27 e Å−3 |
267 parameters |
Experimental. The intensity data was collected on a Bruker X8 Apex II 4 K diffractometer using an exposure time of 60 s/frame. A total of 901 frames were collected with a frame width of 0.5° covering up to θ = 28.36° with 97.9% completeness accomplished. 1H NMR (300 MHz, CDCl3): δ 3.86 (3H, s, CH3), 6.23 (1H, s, CH), 7.00 (2H, d, 3J = 9 Hz, C6H4), 7.49 (6H, m, C6H5), 7.86 (2H, d, 3J = 9 Hz, C6H4), 7.98 (4H, m, C6H5) |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.8626 (2) | −0.0769 (2) | 0.87218 (10) | 0.0320 (5) | |
H1A | 0.9523 | −0.0507 | 0.8606 | 0.048* | |
H1B | 0.8652 | −0.1689 | 0.8913 | 0.048* | |
H1C | 0.8322 | −0.0143 | 0.9075 | 0.048* | |
C2 | 0.7033 (2) | 0.0431 (2) | 0.79677 (9) | 0.0174 (4) | |
C3 | 0.6112 (2) | 0.03525 (19) | 0.73157 (9) | 0.0170 (4) | |
C4 | 0.6122 (2) | −0.0731 (2) | 0.68468 (9) | 0.0182 (4) | |
H4 | 0.6729 | −0.1458 | 0.6944 | 0.022* | |
C5 | 0.5251 (2) | −0.0754 (2) | 0.62396 (9) | 0.0185 (4) | |
H5 | 0.5262 | −0.1496 | 0.5922 | 0.022* | |
C6 | 0.43590 (19) | 0.03071 (19) | 0.60923 (9) | 0.0167 (4) | |
C7 | 0.4309 (2) | 0.1366 (2) | 0.65741 (9) | 0.0202 (4) | |
H7 | 0.3668 | 0.2066 | 0.6491 | 0.024* | |
C8 | 0.5196 (2) | 0.1393 (2) | 0.71743 (9) | 0.0201 (4) | |
H8 | 0.518 | 0.2132 | 0.7494 | 0.024* | |
C9 | 0.2842 (2) | 0.12645 (19) | 0.51204 (9) | 0.0175 (4) | |
C10 | 0.3341 (2) | 0.27011 (19) | 0.52410 (9) | 0.0173 (4) | |
C11 | 0.2415 (2) | 0.37359 (19) | 0.54751 (9) | 0.0174 (4) | |
C12 | 0.1182 (2) | 0.3377 (2) | 0.57072 (10) | 0.0220 (4) | |
H12 | 0.0916 | 0.2456 | 0.5706 | 0.026* | |
C13 | 0.0348 (2) | 0.4364 (2) | 0.59396 (10) | 0.0246 (4) | |
H13 | −0.049 | 0.4119 | 0.6099 | 0.029* | |
C14 | 0.0731 (2) | 0.5703 (2) | 0.59405 (10) | 0.0232 (4) | |
H14 | 0.0155 | 0.6379 | 0.61 | 0.028* | |
C15 | 0.1960 (2) | 0.6065 (2) | 0.57080 (10) | 0.0239 (5) | |
H15 | 0.2217 | 0.6989 | 0.5706 | 0.029* | |
C16 | 0.2802 (2) | 0.5091 (2) | 0.54814 (9) | 0.0192 (4) | |
H16 | 0.3645 | 0.534 | 0.533 | 0.023* | |
C17 | 0.1881 (2) | 0.1073 (2) | 0.45782 (9) | 0.0184 (4) | |
H17 | 0.1429 | 0.1845 | 0.4379 | 0.022* | |
C18 | 0.1510 (2) | −0.0242 (2) | 0.42880 (9) | 0.0190 (4) | |
C19 | 0.0453 (2) | −0.02757 (19) | 0.36781 (9) | 0.0180 (4) | |
C20 | −0.0602 (2) | 0.0635 (2) | 0.36431 (10) | 0.0229 (4) | |
H20 | −0.0665 | 0.1277 | 0.4012 | 0.028* | |
C21 | −0.1566 (2) | 0.0614 (2) | 0.30726 (11) | 0.0274 (5) | |
H21 | −0.2288 | 0.1237 | 0.3052 | 0.033* | |
C22 | −0.1475 (2) | −0.0312 (2) | 0.25364 (11) | 0.0306 (5) | |
H22 | −0.2125 | −0.0317 | 0.2142 | 0.037* | |
C23 | −0.0439 (2) | −0.1231 (2) | 0.25727 (11) | 0.0299 (5) | |
H23 | −0.0386 | −0.1875 | 0.2205 | 0.036* | |
C24 | 0.0531 (2) | −0.1223 (2) | 0.31447 (10) | 0.0236 (4) | |
H24 | 0.124 | −0.1862 | 0.3169 | 0.028* | |
N | 0.35095 (17) | 0.02378 (17) | 0.54652 (8) | 0.0185 (4) | |
O1 | 0.77149 (15) | −0.07201 (15) | 0.80900 (7) | 0.0256 (4) | |
O2 | 0.71416 (15) | 0.14014 (14) | 0.83548 (7) | 0.0235 (3) | |
O3 | 0.44788 (14) | 0.29599 (14) | 0.51058 (7) | 0.0209 (3) | |
O4 | 0.20445 (15) | −0.13062 (14) | 0.45119 (7) | 0.0253 (3) | |
H1 | 0.327 (2) | −0.056 (2) | 0.5293 (11) | 0.022 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0344 (14) | 0.0390 (13) | 0.0206 (9) | 0.0117 (11) | −0.0092 (9) | 0.0008 (9) |
C2 | 0.0166 (10) | 0.0200 (10) | 0.0156 (8) | −0.0012 (8) | 0.0014 (7) | 0.0044 (7) |
C3 | 0.0186 (10) | 0.0176 (10) | 0.0149 (8) | −0.0002 (8) | 0.0025 (7) | 0.0025 (6) |
C4 | 0.0193 (10) | 0.0172 (9) | 0.0183 (8) | 0.0036 (8) | 0.0019 (7) | 0.0034 (7) |
C5 | 0.0226 (11) | 0.0166 (9) | 0.0165 (8) | −0.0006 (8) | 0.0031 (7) | −0.0011 (7) |
C6 | 0.0163 (10) | 0.0186 (9) | 0.0149 (8) | −0.0010 (8) | 0.0004 (7) | 0.0025 (7) |
C7 | 0.0240 (11) | 0.0189 (10) | 0.0177 (8) | 0.0062 (8) | 0.0014 (8) | 0.0007 (7) |
C8 | 0.0259 (11) | 0.0193 (10) | 0.0151 (8) | 0.0017 (8) | 0.0023 (7) | −0.0006 (7) |
C9 | 0.0178 (10) | 0.0194 (10) | 0.0155 (8) | 0.0004 (8) | 0.0028 (7) | −0.0008 (7) |
C10 | 0.0196 (10) | 0.0199 (10) | 0.0117 (7) | −0.0006 (8) | −0.0036 (7) | 0.0010 (7) |
C11 | 0.0200 (10) | 0.0191 (10) | 0.0127 (7) | 0.0010 (8) | −0.0017 (7) | 0.0002 (6) |
C12 | 0.0230 (11) | 0.0215 (10) | 0.0217 (9) | −0.0011 (8) | 0.0029 (8) | −0.0008 (7) |
C13 | 0.0210 (11) | 0.0275 (11) | 0.0260 (9) | 0.0023 (9) | 0.0062 (8) | 0.0005 (8) |
C14 | 0.0247 (12) | 0.0223 (10) | 0.0226 (9) | 0.0078 (9) | 0.0027 (8) | 0.0009 (8) |
C15 | 0.0310 (12) | 0.0177 (10) | 0.0227 (9) | 0.0027 (9) | −0.0005 (8) | 0.0019 (7) |
C16 | 0.0201 (11) | 0.0203 (10) | 0.0169 (8) | −0.0004 (8) | 0.0005 (7) | 0.0021 (7) |
C17 | 0.0196 (11) | 0.0160 (9) | 0.0189 (8) | 0.0001 (8) | −0.0017 (7) | 0.0001 (7) |
C18 | 0.0193 (10) | 0.0201 (10) | 0.0174 (8) | −0.0021 (8) | 0.0009 (7) | −0.0009 (7) |
C19 | 0.0194 (10) | 0.0180 (9) | 0.0166 (8) | −0.0070 (8) | 0.0015 (7) | 0.0015 (7) |
C20 | 0.0221 (11) | 0.0217 (10) | 0.0247 (9) | −0.0040 (9) | 0.0007 (8) | −0.0033 (8) |
C21 | 0.0177 (11) | 0.0303 (12) | 0.0332 (10) | −0.0011 (9) | −0.0026 (9) | −0.0003 (9) |
C22 | 0.0243 (12) | 0.0440 (14) | 0.0224 (9) | −0.0079 (10) | −0.0039 (9) | −0.0023 (9) |
C23 | 0.0310 (13) | 0.0358 (13) | 0.0227 (9) | −0.0061 (10) | 0.0014 (9) | −0.0108 (9) |
C24 | 0.0255 (12) | 0.0223 (11) | 0.0233 (9) | −0.0015 (9) | 0.0041 (8) | −0.0032 (8) |
N | 0.0235 (10) | 0.0158 (8) | 0.0157 (7) | 0.0000 (7) | −0.0020 (7) | −0.0019 (6) |
O1 | 0.0293 (9) | 0.0290 (8) | 0.0171 (6) | 0.0100 (7) | −0.0065 (6) | −0.0011 (5) |
O2 | 0.0290 (9) | 0.0210 (8) | 0.0199 (6) | −0.0029 (6) | −0.0025 (6) | −0.0006 (5) |
O3 | 0.0180 (8) | 0.0235 (8) | 0.0209 (6) | −0.0018 (6) | 0.0005 (5) | −0.0027 (5) |
O4 | 0.0313 (9) | 0.0179 (7) | 0.0256 (7) | 0.0016 (6) | −0.0041 (6) | 0.0014 (5) |
C1—O1 | 1.444 (2) | C12—C13 | 1.383 (3) |
C1—H1A | 0.98 | C12—H12 | 0.95 |
C1—H1B | 0.98 | C13—C14 | 1.378 (3) |
C1—H1C | 0.98 | C13—H13 | 0.95 |
C2—O2 | 1.207 (2) | C14—C15 | 1.392 (3) |
C2—O1 | 1.338 (2) | C14—H14 | 0.95 |
C2—C3 | 1.481 (2) | C15—C16 | 1.375 (3) |
C3—C8 | 1.390 (3) | C15—H15 | 0.95 |
C3—C4 | 1.393 (3) | C16—H16 | 0.95 |
C4—C5 | 1.384 (2) | C17—C18 | 1.448 (3) |
C4—H4 | 0.95 | C17—H17 | 0.95 |
C5—C6 | 1.392 (3) | C18—O4 | 1.240 (2) |
C5—H5 | 0.95 | C18—C19 | 1.501 (3) |
C6—C7 | 1.393 (3) | C19—C24 | 1.386 (3) |
C6—N | 1.404 (2) | C19—C20 | 1.388 (3) |
C7—C8 | 1.384 (3) | C20—C21 | 1.388 (3) |
C7—H7 | 0.95 | C20—H20 | 0.95 |
C8—H8 | 0.95 | C21—C22 | 1.377 (3) |
C9—N | 1.353 (2) | C21—H21 | 0.95 |
C9—C17 | 1.361 (3) | C22—C23 | 1.378 (3) |
C9—C10 | 1.517 (3) | C22—H22 | 0.95 |
C10—O3 | 1.220 (2) | C23—C24 | 1.394 (3) |
C10—C11 | 1.476 (3) | C23—H23 | 0.95 |
C11—C12 | 1.395 (3) | C24—H24 | 0.95 |
C11—C16 | 1.396 (3) | N—H1 | 0.88 (2) |
O1—C1—H1A | 109.5 | C14—C13—H13 | 119.9 |
O1—C1—H1B | 109.5 | C12—C13—H13 | 119.9 |
H1A—C1—H1B | 109.5 | C13—C14—C15 | 120.08 (19) |
O1—C1—H1C | 109.5 | C13—C14—H14 | 120 |
H1A—C1—H1C | 109.5 | C15—C14—H14 | 120 |
H1B—C1—H1C | 109.5 | C16—C15—C14 | 120.3 (2) |
O2—C2—O1 | 123.59 (17) | C16—C15—H15 | 119.9 |
O2—C2—C3 | 124.49 (18) | C14—C15—H15 | 119.9 |
O1—C2—C3 | 111.90 (16) | C15—C16—C11 | 119.8 (2) |
C8—C3—C4 | 119.20 (17) | C15—C16—H16 | 120.1 |
C8—C3—C2 | 118.48 (17) | C11—C16—H16 | 120.1 |
C4—C3—C2 | 122.32 (17) | C9—C17—C18 | 123.66 (18) |
C5—C4—C3 | 120.29 (18) | C9—C17—H17 | 118.2 |
C5—C4—H4 | 119.9 | C18—C17—H17 | 118.2 |
C3—C4—H4 | 119.9 | O4—C18—C17 | 122.89 (17) |
C4—C5—C6 | 120.24 (17) | O4—C18—C19 | 120.07 (17) |
C4—C5—H5 | 119.9 | C17—C18—C19 | 117.03 (17) |
C6—C5—H5 | 119.9 | C24—C19—C20 | 119.69 (18) |
C5—C6—C7 | 119.59 (17) | C24—C19—C18 | 119.77 (18) |
C5—C6—N | 117.80 (17) | C20—C19—C18 | 120.54 (17) |
C7—C6—N | 122.58 (17) | C21—C20—C19 | 120.32 (19) |
C8—C7—C6 | 119.82 (18) | C21—C20—H20 | 119.8 |
C8—C7—H7 | 120.1 | C19—C20—H20 | 119.8 |
C6—C7—H7 | 120.1 | C22—C21—C20 | 120.0 (2) |
C7—C8—C3 | 120.77 (18) | C22—C21—H21 | 120 |
C7—C8—H8 | 119.6 | C20—C21—H21 | 120 |
C3—C8—H8 | 119.6 | C21—C22—C23 | 119.96 (19) |
N—C9—C17 | 123.33 (18) | C21—C22—H22 | 120 |
N—C9—C10 | 119.14 (16) | C23—C22—H22 | 120 |
C17—C9—C10 | 116.57 (16) | C22—C23—C24 | 120.58 (19) |
O3—C10—C11 | 122.91 (18) | C22—C23—H23 | 119.7 |
O3—C10—C9 | 117.87 (17) | C24—C23—H23 | 119.7 |
C11—C10—C9 | 119.12 (17) | C19—C24—C23 | 119.5 (2) |
C12—C11—C16 | 119.70 (18) | C19—C24—H24 | 120.3 |
C12—C11—C10 | 121.16 (18) | C23—C24—H24 | 120.3 |
C16—C11—C10 | 119.12 (18) | C9—N—C6 | 127.71 (17) |
C13—C12—C11 | 119.97 (19) | C9—N—H1 | 112.7 (14) |
C13—C12—H12 | 120 | C6—N—H1 | 119.1 (14) |
C11—C12—H12 | 120 | C2—O1—C1 | 116.72 (16) |
C14—C13—C12 | 120.1 (2) | ||
O2—C2—C3—C8 | −7.7 (3) | C13—C14—C15—C16 | −0.5 (3) |
O1—C2—C3—C8 | 170.72 (18) | C14—C15—C16—C11 | 0.9 (3) |
O2—C2—C3—C4 | 173.1 (2) | C12—C11—C16—C15 | −0.8 (3) |
O1—C2—C3—C4 | −8.5 (3) | C10—C11—C16—C15 | −179.03 (16) |
C8—C3—C4—C5 | 1.5 (3) | N—C9—C17—C18 | −3.0 (3) |
C2—C3—C4—C5 | −179.27 (18) | C10—C9—C17—C18 | 165.61 (18) |
C3—C4—C5—C6 | 0.1 (3) | C9—C17—C18—O4 | −0.1 (3) |
C4—C5—C6—C7 | −2.6 (3) | C9—C17—C18—C19 | −178.55 (18) |
C4—C5—C6—N | 179.32 (18) | O4—C18—C19—C24 | −33.9 (3) |
C5—C6—C7—C8 | 3.7 (3) | C17—C18—C19—C24 | 144.54 (19) |
N—C6—C7—C8 | −178.39 (18) | O4—C18—C19—C20 | 146.1 (2) |
C6—C7—C8—C3 | −2.1 (3) | C17—C18—C19—C20 | −35.4 (3) |
C4—C3—C8—C7 | −0.4 (3) | C24—C19—C20—C21 | −0.9 (3) |
C2—C3—C8—C7 | −179.72 (18) | C18—C19—C20—C21 | 178.98 (19) |
N—C9—C10—O3 | 58.6 (2) | C19—C20—C21—C22 | −0.2 (3) |
C17—C9—C10—O3 | −110.5 (2) | C20—C21—C22—C23 | 1.1 (3) |
N—C9—C10—C11 | −124.84 (18) | C21—C22—C23—C24 | −0.8 (4) |
C17—C9—C10—C11 | 66.0 (2) | C20—C19—C24—C23 | 1.2 (3) |
O3—C10—C11—C12 | −172.08 (17) | C18—C19—C24—C23 | −178.67 (19) |
C9—C10—C11—C12 | 11.6 (2) | C22—C23—C24—C19 | −0.4 (3) |
O3—C10—C11—C16 | 6.1 (3) | C17—C9—N—C6 | −169.39 (19) |
C9—C10—C11—C16 | −170.22 (16) | C10—C9—N—C6 | 22.2 (3) |
C16—C11—C12—C13 | 0.2 (3) | C5—C6—N—C9 | −160.62 (19) |
C10—C11—C12—C13 | 178.45 (17) | C7—C6—N—C9 | 21.4 (3) |
C11—C12—C13—C14 | 0.2 (3) | O2—C2—O1—C1 | −0.3 (3) |
C12—C13—C14—C15 | −0.1 (3) | C3—C2—O1—C1 | −178.74 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
N—H1···O4 | 0.88 (2) | 1.99 (2) | 2.703 (2) | 138 (2) |
C1—H1B···O3i | 0.98 | 2.55 | 3.068 (2) | 113 |
C1—H1C···O2 | 0.98 | 2.31 | 2.671 (3) | 101 |
C4—H4···O2i | 0.95 | 2.49 | 3.368 (2) | 154 |
C5—H5···O3ii | 0.95 | 2.46 | 3.386 (2) | 165 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) −x+1, −y, −z+1. |
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